The present invention relates to branched ketones of the genus of compounds having the structure: ##STR2## wherein R.sub.4 ' represents C.sub.1 -C.sub.4 lower alkyl; wherein one of the dashed lines is a carbon-carbon double bond and the other of the dashed lines represents carbon-carbon single bonds, produced by the novel process of our invention, and to novel compositions using one or more of such branched ketones to augment or enhance the flavor and/or aroma of consumable materials, or impart flavor and/or aroma to consumable materials.
There has been considerable work performed relating to substances which can be used to impart (modify, augment or enhance) flavors and fragrances to (or in) various consumable materials. These substances are used to diminish the use of natural materials, some of which may be in short supply, and to provide more uniform properties in the finished product.
Woody, citrus, floral, ionone-like, incense-like, oriental, grapefruit-like, piney, fruity and rosin-like aromas with woody, citrusy, floral, ionone-like, oriental, grapefruit-like, piney, fruity and rosin-like tastes with bitter undertones are particularly desirable for many uses in foodstuff flavors, chewing gum flavors, toothpaste flavors, medicinal products flavors and chewing tobacco flavors.
Sweet, woody, oriental-like, camphoraceous, fruity and spicey aromas prior to smoking and woody, peppery and oriental-like aromas with natural tobacco nuances on smoking in the main-stream and in the side-stream are desirable in smoking tobaccos, smoking tobacco articles and in smoking tobacco flavoring compositions.
Fruity, warm, woody, amber, rum/cognac-like, sandalwood-like, sweet, floral, rich woody, vetiver-like, aromas with patchouli top-notes and minty undertones, are highly desirable in several types of perfume compositions, perfumed articles and colognes.
Unsaturated ketones including unsaturated branched aliphatic, acyclic ketones are well known for use in augmenting or enhancing the aroma and/or taste of consumable materials. Thus, Arctander, "Perfume & Flavor Chemicals (Aroma Chemicals)", published 1969, discloses at monograph No. 472, the use of butylidene acetone having the structure: ##STR3## Arctander states that butylidene acetone has a powerful, grassy, green, pungent odor and a rather poor tenacity. At monograph 2427, Vol. 2, Arctander states that Octylidene acetone having the structure: ##STR4## is useful in Jasmin compositions as a modifier for Amylcinnamic aldehyde, or in Gardenia and other heavy floral perfumes, where herbaceous-fruity notes are desirable and compatible with the fragrance picture.
U.S. Pat. No. 2,315,046 discloses the use as ingredients in perfumery of certain acylated olefins, which olefins have structures such as: ##STR5##
These materials are prepared interalia from commercial diisobutylene according to the reaction: ##STR6## wherein n is 3 or more, and R represents a hydrocarbon radical. Branched unsaturated alpha-beta ketones were known prior to that, for example, in U.S. Pat. No. 2,246,032, issued on June 17, 1941, disclosing compounds having the generic structure: ##STR7## wherein R.sub.1 -R.sub.7 may be any member of the group consisting of hydrogen, aliphatic and cyclo paraffinic.
Also, claimed in U.S. Pat. No. 2,315,046 are compounds having the structures: ##STR8##
In addition, U.S. Pat. No. 2,463,742 discloses the reaction: ##STR9##
U.S. Pat. No. 3,453,317, issued on July 1, 1969, discloses certain gamma, delta unsaturated ketones as odorants for perfumery purposes at Column 4, line 33 including the group of ketones having the structure: ##STR10## wherein R.sub.1 -R.sub.5 are various hydrocarbon radicals.
U.S. Pat. No. 2,870,210, discloses as having aromas such as fruity, "reminiscent of apple juice" the compound 6,8-dimethyl-5-nonene-2-one having the structure: ##STR11## as well as 6,10-dimethyl-5-undecane-2-one having the structure: ##STR12##
Nothing in the prior art specifically discloses the genus of compounds having the structure: ##STR13## wherein R.sub.4 ' represents C.sub.1 -C.sub.3 lower alkyl; wherein one of the dashed lines represents a carbon-carbon double bond and the other of the dashed lines represents a carbon-carbon single bond. And nothing in the prior art discloses the generic process: ##STR14## wherein R.sub.1 ', R.sub.2 ' and R.sub.3 ' are the same or different and each represents C.sub.1 -C.sub.3 lower alkyl; wherein R.sub.4 ' is as defined above and wherein X is chloro or bromo. Indeed, the compounds and processes of our invention give rise to unexpected, unobvious and advantageous utilities insofar as organoleptic uses are concerned.